The objective for the overall program is the synthesis of the antitumor antibiotic, Streptonigrin (1). This is being approached in stages, the first being the synthesis of destrioxyphenylstreptonigrin 2 (i.e., 1 without the D-ring). We are close to meeting this objective. Based on the above experience, the next stage will be the synthesis of selected analogues of 2 in which modifications in the B- and C-rings will be made. Specifically, the quinoline system of 2 will be replaced by a quinoxaline and two types of isoquinoline systems. Similarly, as C-ring variants, compounds in which the COOH and the CH3 groups of 2 are replaced by other substituents are planned. Evaluation of these analogues will provide valuable correlative data. The third stage will be the synthesis of streptonigrin itself. This will require the preparation of the key intermediate with the phenyl-pyridine system with the typical substitution pattern of the C- and D-rings of the compound. Once this is accomplished, subsequent steps follow the procedures used in connection with the synthesis of 2.